Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diethylamine | HCID 8021 | — |
| Reactant | Propylphosphoric anhydride | HCID 16167369 | — |
| Reactant | 1-methyl-5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid | HCID 57378954 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 57377522 | HCID 57377522 | 80.7% |
Reaction Steps
A mixture of 1-methyl-5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid (100 mg, 276 μmol), diethylamine (142 μl, 1.38 mmol) and propylphosphonic anhydride (50% in ethyl acetate, 407 μl, 690 μmol) in tetrahydrofurane (7 ml) is stirred for 20 hours at 70° C. under nitrogen atmosphere. The solvent is evaporated and to the residue is added sat. aqueous sodium hydrogencarbonate solution. The mixture is stirred for 20 minutes while a white solid precipitates. The solid is collected by filtration, washed with diethylether and dried affording N4,N4-diethyl-1-methyl-N5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1H-pyrazole-4,5-dicarboxamide (93 mg, 80.7%) as a white solid. mp.: 177-9° C. MS: m/z=418.3 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08349824B2 |
|---|
| Source dataset | uspto-grants-2013_01 |
|---|
| ORD ID | ord-576f467ebd71428fb58732e37ca94ae9 |
|---|
| Source note | uspto-grants-2013_01 |
|---|